Why I Left My 9 to 5 for a Startup Making No Money

Leaving your full-time job for a start up is never an easy decision. The security that a 9 to 5 brings keeps most people from testing the startup waters. Making the decision for me was not an easy one, but it was essential to my growth as an entrepreneur, and more importantly to my growth as a man.

I was working a full-time job for the City of Toronto, as a special assistant to the now internationally known, and former Mayor of Toronto, Rob Ford.

I really liked the job I was doing, it was a challenging job that kept me on my toes and allowed me to meet people from all walks of life. Working for the person who is in charge of Canada’s largest city is no small task, and requires you to be “on” 24 hours a day.

At the time, CAVE Social was a side-project for me, it wasn’t getting the attention that it needed for it to be a successful company. I was aware of the potential of CAVE, but I did not commit the energy, nor time to it to make it a success. This is when it all hit me, if I worked as hard as I did for myself as I did for Rob Ford, there was no reason CAVE Social would not be a success.

Within a few weeks I informed the staff I would be leaving to pursue my entrepreneurial desires.

Our first office, a college bedroom.

Here are a few tips which helped me through my transition from employee to entrepreneur.

1. Have a Plan

Set a timetable for yourself to make the transition easier. Leaving your job will be tough, but to enter in to a world where you are now your own boss will be even tougher. You should have a plan as to what objectives you need to complete on a daily and weekly basis. A useful exercise is to write down five short-term goals (90 days) and a road map to achieve them. This exercise helped me stay focused on my goals, both personally and with business.

In our early days at an event for the magazine.

2. Don’t Do It Alone

Having the courage to start your own company is something few of us choose to do. It is no simple task. More importantly, it’s difficult to do alone. If it is suitable for your company, go into business with a co-founder. It will lessen the burden on yourself and you will have someone who relies on you as much as you rely on them. Moreover, your business partner should have a mindset similar to yours, but a skillset which is different. This differentiation will allow for the burden of your business/growth to be divided where you see fit. You’re also going to need support from the people around you. There are going to be people who don’t believe in the decision you’re making, and advise against it; that’s okay. Spend your time and energy on the people who believe in and support your vision.

3. Save Money

If you are starting your own company in the hopes of becoming a millionaire overnight, save yourself from that idea and stay at your job. If you are starting your own company because you want to create your own work culture and make a difference in whatever industry it is, prepare to have financial ups and downs. One thing that helped me was saving up some money before leaving the Mayor’s Office. I did this because I knew CAVE was making little revenue, and we were dumping everything we made back into the company. I knew it would be a grind and I welcomed the challenge.

First company retreat to Las Vegas in 2014. Truly a surreal experience.

4. Keep Your Routine Consistent

If you were getting up at 6:00 am everyday to get to your old job, don’t change that. When you work for yourself, it is easy to repeatedly hit the snooze button and wake up at 11:00 am everyday. Stay committed to a plan, get up, and get after it.

It took me a couple days to realize, but when I was working with the Mayor, I was up at 5:00 am everyday and when I left I wasn’t waking up until 10:00 am. I realized that if I could wake up 5:00 am everyday to help someone else live their dream, I sure as hell better be able to do it for myself.

If you’re thinking about starting your business or joining a startup, I’d love to hear about it and offer any advice I can. Feel free to connect with me on LinkedIn.

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